Molecules 2013, 18(9), 11496-11511; doi:10.3390/molecules180911496
Article

Synthesis and Biological Evaluation of Apigenin Derivatives as Antibacterial and Antiproliferative Agents

1,2, 2, 1, 1, 1, 1,* email and 1,* email
Received: 8 July 2013; in revised form: 2 September 2013 / Accepted: 12 September 2013 / Published: 17 September 2013
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: Two series of apigenin [5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one] derivatives, 3a3j and 4a4j, were synthesized. The apigenin and alkyl amines moieties of these compounds were separated by C2 or C3 spacers, respectively. The chemical structures of the apigenin derivatives were confirmed using 1H-NMR, 13C-NMR, and electrospray ionization mass spectroscopy. The in vitro antibacterial and antiproliferative activities of all synthesized compounds were determined. Among the tested compounds, 4a4j displayed significant antibacterial activity against the tested strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa). Additionally, 4i showed the best inhibitory activity with minimum inhibitory concentrations of 1.95, 3.91, 3.91, and 3.91 μg/mL against S. aureus, B. subtilis, E. coli, and P. aeruginosa, respectively. The antiproliferative activity of the apigenin derivatives was evaluated by an MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide] assay. We determined that 4a4j displayed better growth inhibition activity against four human cancer cell lines, namely, human lung (A549), human cervical (HeLa), human hepatocellular liver (HepG2), and human breast (MCF-7) cancer cells, than the parent apigenin. Compound 4j was found to be the most active antiproliferative compound against the selected cancer cells. Structure-activity relationships were also discussed based on the obtained experimental data.
Keywords: synthesis; biological evaluation; apigenin derivatives; antibacterial activity; antiproliferative activity; MTT assay
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MDPI and ACS Style

Liu, R.; Zhang, H.; Yuan, M.; Zhou, J.; Tu, Q.; Liu, J.-J.; Wang, J. Synthesis and Biological Evaluation of Apigenin Derivatives as Antibacterial and Antiproliferative Agents. Molecules 2013, 18, 11496-11511.

AMA Style

Liu R, Zhang H, Yuan M, Zhou J, Tu Q, Liu J-J, Wang J. Synthesis and Biological Evaluation of Apigenin Derivatives as Antibacterial and Antiproliferative Agents. Molecules. 2013; 18(9):11496-11511.

Chicago/Turabian Style

Liu, Rui; Zhang, Hongchi; Yuan, Maosen; Zhou, Jiao; Tu, Qin; Liu, Jian-Jun; Wang, Jinyi. 2013. "Synthesis and Biological Evaluation of Apigenin Derivatives as Antibacterial and Antiproliferative Agents." Molecules 18, no. 9: 11496-11511.

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